Chlorosuccinimide → 3-chloro-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Participants

Reaction Steps

To an ice-cold solution of 4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.015 g, 0.071 mmol) in DMF (2 mL), under N2, was added a solution of NCS (0.011 g, 0.079 mmol) in DMF (0.5 mL). The mixture was stirred at rt for 1 h and then heated at 75° C. for 40 min. Upon cooling, the mixture was partitioned between Et2O and 0.1N HCl. The organic phase was washed with water and sat'd brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by radial chromatography (50-100% CH2Cl2 hexanes gradient, followed by 1-5% MeOH—CH2Cl2 gradient) to afford the title compound (0.014 g, 82% yield): MS (ES) m/z 245 (M+1).

Provenance & Evidence